A Real Dilemma
by JWolf28
Summary: Oliver goes out one night to stop a villain named Dilemma. The only problem is that she seems to think they're best friends. AU where Felicity is a little crazy and villain-y and Oliver just wants her to go home.
1. Chapter 1

**A/N: So, I'm back! I know it's been a while since I wrote anything, but I saw a post on Pinterest from a Tumblr thread about if a villain thought they were best friends with the hero and this just came to life. A few lines in this are bolded and those are the lines that were taken nearly word for word from the post. Anyway, I could add more to this if anyone is interested. Let me know in the reviews!**

Thunder rumbled in the distance as Oliver entered the bank. The lobby was dark save for a light coming from inside the office, drawing the hooded vigilante closer to the door. He didn't raise his bow, knowing exactly who was inside. He pushed the door open and stood there silently for a moment, watching the young woman rifle through the desk drawers. "I thought you didn't go out during storms."

She jumped, blonde ponytail swaying as she spun around to look at him. "Jesus, Hoodie, you scared me."

His eye twitched in annoyance. "It's Arrow, Smoak."

She sighed heavily. "How many times do I have to tell you? It's Dilemma when I'm working. Gosh, Hoodsie, I knew you were dense, but I didn't think it was _that_ bad. It's really only curtesy, you know. I don't call you by your name when you're all dressed up."

He rolled his eyes. "Come on, you need to go back to Iron Heights."

She pouted, full lips turning down in a frown under black lipstick. "You didn't even drink the latte I brought you!"

Oliver looked at the cup she was pointing at and picked it up, turning it so he could see the name. **"This doesn't have either of our names on it."**

 **"No one grabbed it for, like, a minute after the barista called it. I didn't want it to go to waste!"**

"Whatever. We need to get going unless you want to get caught in this storm."

She squeaked in alarm, gathering her things before running to him, clutching his arm in alarm. "There's a storm? It wasn't in the forecast! I didn't hear anything coming in. Are you sure it's safe?"

Oliver shook her off his arm. "It's fine." He quickly cuffed her and led her out to the police car that waited, passing her off to Detective Lance, who only sighed and shoved her into the backseat. As the car pulled away, she waved at him and the vigilante frowned in thought. There was a reason she called herself Dilemma. There was always a choice and it usually involved arresting her or stopping a crime. He'd only arrested her. What had the other choice been?

He got his answer the next morning. Three banks had been robbed while he's been talking to her, _and_ she somehow escaped from the back of Lance's car en route to the station. There hadn't been any indication of the villainess' plot this time and Oliver made a mental note to talk to her about it next time he saw her. Because there would always be a next time. He didn't see her stopping her little game anytime soon, and she stopped by Queen Consolidated at least once a week with lunch for the two of them. For whatever reason, she seemed to think they were friends. Where she got the idea, he had no clue, but it was more than a little frustrating when he knew he couldn't turn her in when she did that because the public didn't know Dilemma's name. Somehow, the blonde genius had kept it from coming up, no matter how many times it was added to her file at the station. If Oliver Queen knew that Felicity Smoak and Dilemma were one and the same, it would be obvious that something was up. He couldn't risk it.

As he watched the news, he thought about the first time he'd met her. At the time, she'd been working at Merlyn Global as an IT girl. A certified genius, she'd graduated from MIT at only nineteen and was hired at MG immediately after graduation. Oliver had met her when he'd gone to see Tommy and had been redirected to her office, where she was fixing his friend's computer. At the time, she'd been normal. No thieving tendencies, no urge to destroy things. A model citizen. However, when she'd been a MG for two years, she'd been walking home during a rain storm and had gotten struck by lightning. She'd been a coma for three days with major brain damage, only waking up when she went into cardiac arrest and got shocked back to life.

Almost immediately, she'd broken out of the hospital and the next time Oliver saw her, she was decked out in her Dilemma costume. A far cry from the colorful woman he'd known, she now wore a black T-shirt underneath a black leather jacket, paired with black skinny jeans, and black high heeled ankle boots. The only color in her outfit was on her face, which was painted white, her eyes and lips painted black, and her eyebrows filled in with the same color. One red line stretched diagonally from the top of her forehead to her chin. The effect was chilling and the residents of Starling City had learned to fear her, especially after her first heist, which ended with the bombing of City Hall. No one had died- that clearly hadn't been the intent- but the damage shut the mayor's office down for months and destroying a ton of information.

Oliver was knocked out of his reverie by the doorbell and moved to answer it. When the door swung open, he growled angrily at the person on his doorstep. "What are you doing here? We're enemies!"

Felicity ignored him, slipping past him into the apartment. **"I got us a groupon to that new Thai place** by Big Belly."

He scoffed. **"You probably stole it."**

She shrugged. **"It's really the savings that are the crime.** So, you wanna go?"

"No! You're a villain! You robbed three banks last night!"

"Actually, only two. At least, I only planned two, but my crew is good at their jobs. Anyway, I'm hungry and the tuck and roll from that car last night hurt my ribs. You know I like Thai when I'm hurt."

Oliver sighed and rubbed a hand over his face. As much as he wanted to say no, he knew that if he did he would 'hurt her feelings', which meant that she would go on a shopping spree where she held up every shopping center in a ten-mile radius and took what she wanted. "Let me grab my coat."

She hummed happily and spun around in circles while she waited. Only a couple of minutes later, they were in Oliver's new BMW and on their way. As she fiddled with the radio, she said "You're treating."

"Didn't you rob three banks last night?"

"Only two that I know of. And you're a billionaire. I am not. So, it's your treat."

Somehow, he couldn't argue that logic. "Fine. But next time I get to choose the place."

"Deal."

 **A/N 2: If you're curious to what Felicity's face paint looks like, I based it off of Lisbeth Salandar's in The Girl Who Played with fire. Throw that into Google Images and you should be able to find it.**


	2. Chapter 2

The knock on the door made Oliver groan. With his mother in England and with Walter and T hea still upstairs in her room, there was really only one person it could be. As he opened the door, he was proved correct. The blonde grinned widely upon seeing him. "Hey, Oliver! I brought you another latte. And this time, I bought."

He rolled his eyes as he accepted the coffee, saying sarcastically, "I'm so proud."

She smiled wider. "I thought you might be."

"I don't recall having plans today."

"We don't. Thea and I are going shopping."

Oliver frowned. "When did you and Thea become friends?"

"I friended her on Facebook."

"What? Whatever. Why'd you bring me coffee then?"

She giggled. " **I thought you'd be thirsty from trying to stop criminals."**

 **"You're the one usually doing the crime!"**

 **"I'm an artist."**

He rolled his eyes. " **Speaking of art, I've already returned the Wharhol's you gave me."**

Her eyes watered with tears. " **Those were your birthday present.** You didn't like them?"

He started to panic a little internally. He was far too close to hurting her feelings and inciting the shopping spree from hell. " **For one, they were stolen, and I don't even like pop art.** "

The tears disappeared. " **So you want something more art nouveau for Hanukkah, then?** "

He sighed. There was no chance she was going to let this go. "Fine. Whatever."

Felicity brightened and grinned. "Excellent. You are going to LOVE what I have planned for you!"

At that moment, Thea came bounding down the stairs. "Lis, you're here! Bye, Ollie, we'll see you later. I finally found someone who loves shopping as much as I do. And she somehow has the budget for it." Thea frowned at her friend. "Aren't you unemployed?"

"I'm a thief," the blonde deadpanned.

Thea was silent a moment before bursting into laughter. "Isn't she hilarious? I can tell we are going to be great friends."

Oliver pursed his lips as he watched them walk out the door. "Speedy, don't do anything I wouldn't do!"

"So, not much then?" At his sullen glare, she rolled her eyes. "Kidding. I promise I will behave myself perfectly. Right, Lis?"

The villainess grinned. "Oh, don't worry. I'll keep you out of trouble."

Oliver didn't quite believe it, but he knew that Felicity would protect Thea with her life, and that was good enough for him. Of course, the call he got from the police station an hour later, didn't quite cut it.

 **A/N: And there you go! I know it took forever to update a new chapter for this and I am so sorry. Let me know what you think and if you want another chapter! I love hearing from you guys, especially when you have ideas for future chapters. Same as the last chapter, the bolded lines are what I borrowed from the Tumblr thread and I take absolutely no credit for it.**


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